


In Her Hands

by LucifersDominus



Category: Critical Role (Web Series)
Genre: Aftercare, BDSM, Biting, Bondage, Dirty Talk, F/M, Femdom, Healing Kisses, Magic Strap-on, Multiple Orgasms, Orgasm Delay/Denial, Pegging, Praise Kink, Rough Sex, Spanking
Language: English
Status: Completed
Published: 2020-04-28
Updated: 2020-04-28
Packaged: 2021-03-02 01:54:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,223
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23887003
Author URL: https://archiveofourown.org/users/LucifersDominus/pseuds/LucifersDominus
Summary: After weeks on the road unable to do more than fall asleep next to each other Caleb and Jester have time to play, and Jester is going to make sure her sweet wizard remembers his place.or nearly ten pages worth of indulgent loving femdom widojest.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 1
Kudos: 96





	In Her Hands

**Author's Note:**

> Hello everyone! This is my first time writing for Critical Role and the first time in a long time I've actually sat down to write a oneshot and then actually finished it, so I'm really excited to put this out here and I hope you enjoy! 
> 
> Also I love these two so much so I am considering turning this into a series of oneshots so let me know if there's a scenario (doesn't have to be sexual) or kink you'd like to see me do!

Caleb was so handsome on his knees, his usually strung tight frame slowly relaxing with each moment as he settled in the candlelight. The flickering light drew Jester’s attention away from her preparations to watch him for a moment as the shadows danced across sharp cheekbones framed by damp and curling red locks, his full lips parted ever so slightly, the tip of his tongue darting out making them shine as his eyes flicked up for just a moment stealing a peek at his Mistress. 

Normally he was better behaved, but lately, there was too much going on, too much running back and forth from one fight to another. The lack of downtime, of privacy and peace, was wearing on them both, but Caleb more so as each new fight fed the worst of his habits, and while Jester rather found his little disobedience adorable it would not help Caleb to let him get away with it. 

“Eyes down, Cayleb,” she tutted sweetly, walking slowly around him, letting the heel of her boots click satisfyingly with each step and then pressing the tip of one against his back, “and straighten up!”

As Caleb moved to do so Jester gave in to the urge to tangle her fingers in his hair, helping guide him up and then pulling his head back, the soft gasp he let out sending a bolt of pleasure through her. At this angle he couldn’t help but look at her, his gaze a little wild, needy, and a blush creeping across his cheeks as beyond that his cock was straining hard and red. 

Giggling Jester bent over him, pressing her breasts against his face while she reached down to run her fingertips teasingly up and down his shaft. Caleb was practically vibrating, trying to stay still, but when she tightened her grip stroking him, her thumb catching a drop of precum to spread lightly across his tip Caleb’s hips hitched, breath ragged against her skin as he let out a low moan. 

Immediately taking her hand off and straightening up, she tightened her grip on his hair to the point of pain, “Cayleb, you are not being very good... do I need to get the cage?”

Caleb stilled a look of shame crossing over his face quick, swallowing hard before answering, “If that would please you, Mistress,”

“What would please me would be my boy behaving,” Jester kept her grip steady, the literal physical manifestation of the firm hand her sweet wizard needed, “can he do that?”

“ _Ja_ , _Ja_ , Mistress, I just-“ he cut himself off.

Jester waited for a beat to see if Caleb could fight through his insecurity, his lingering need to hold onto control, to ask for what he so clearly needed. Even as he was struggling, that tight grip in his hair and her unwavering demands were settling him and without being told, without even realizing he was doing so, he fixed the other issues with his posture. Spreading his knee’s more, lifting off of his heels, his eyes did not even dart towards her now focused down and away. Still, Jester wanted him to ask, to hand over that last bit of control over himself and open himself to her body, mind, and soul. 

They both wouldn’t be satisfied until he did. Caleb knew that as much as Jester did. If he would just admit he needed help, it would be easier but Jester knew that was still difficult at the best of times but after weeks with no time for more than wrapping around the other to sleep, where his headspace was so constantly solidly on the group and their goals, it might be impossible for her boy. 

When he stayed silent, Jester sighed, clicking her tongue and releasing his hair. 

“You know Cayleb I had such lovely plans for tonight, but I can see you’re just going to be difficult,”

Jester crossed the room, a dozen different ideas swirling in her mind, so many delicious options for cracking that rigidly held control, so many ways to pull Caleb’s submission out. But which one tonight?

Caleb was trying, she did see that, this was not one of those times he was consciously disobeying -those were very few and very far between, he really was a good boy for her- and she could feel the tumultuous emotions raging in him behind her as she looked over their toys. Each one had been carefully discussed by them before purchasing, and Jester knew exactly what reaction each would cause in Caleb. A set of ropes they rarely used though -largely her fault, Jester would admit, patience had never been her virtue and the enchanted cuffs that locked with just a word were much quicker- jumped out at her and Jester was very glad he couldn’t see the grin that stretched across her face as a plan solidified in her mind.

Oh yes, they would work quite nicely.

“Get on the bed, on your knees with your head down,”

There was no answer but Jester could hear as he moved quickly into position as she gathered everything she needed. Jester decided to draw it out, let him stew just a little in mostly silence as she hummed and took her time. It would give Caleb’s ever-turning mind time to drive him just a little crazy wondering what was about to happen, build the anticipation of her touch, her dominance over him.

“Do you want to know what I’m going to do to you Cayleb?” Her tone was sweet and cheery as she finally turned to him, taking in every line of his prone form.

A heartbeat passed, then softly, “Please,”

“Please what Cayleb?”

“Please, Mistress, please I... I...”

Jester tsked, sharpening her voice just a touch, “That’s not an answer to my question,”

“Yes, please, Mistress,”

“Good! See I am going to bind you and your pretty cock up nice and tight so you can’t move at all,” Jester started unfurling the rope as she talked, first just laying it against his skin before she began to loop and tie it around him, binding wrist to wrist up to the headboard, following down his arms, tying them together as well and cooing slightly letting her fingers linger against his skin after each knot. 

Slowly she made her way down Caleb’s stiffened body, murmuring to him as she spread his slightly resistant legs tying each ankle to either side of the footboard but keeping his knees pressed under him bound to the ropes around his stomach, leaving him completely open to her, “There just like that, try and wiggle for me, Cayleb,”

He did, unable to move in any way, his breath which had steadied as she worked picking up.

“Is anything too tight?”

Caleb only shook his head.

Quick as a whip, Jester spanked him none-too-gently, on that pretty too pale ass, “I need your words, Cayleb,”

“Ah! I- I am good, _Ja_ ,  _ grün _ ,”

Jester hummed happily, gently stroking where her handprint was already rising, “I’m glad because now I am going to warm your tight little ass before I fill it,”

Caleb whimpered, pressing as much as he could back against her.

“And then,” Jester trailed that word out as she first bound his cock and balls tight with a strip of matching leather, then leaned over him, reveling in the press of his rope trussed body against her fingers tracing each line as she whispered low in his ear, “I am going to make you watch me make myself cum, over and over again until you decide to be my good boy again,”

Caleb’s breath caught, “Nein, Nein Mistress, please, let me-”

“Nope!” Jester popped the P as she straightened and didn’t give him a moment more to think let alone beg as she began to spank him. This had been part of her original plan, and there was no need to throw all of that away when it pleased her so much to feel his skin warm beneath her palm. It would settle him too, the heat, the pain, with the ropes it would all send him out of his head until he was purely in the moment with her.

So Jester set her strikes quick and hard from the start, loving every little sound he made as her hand came down again and again. At first, with no rhythm for him to latch onto, nothing he could predict or brace for, hoping maybe this would be enough for her boy to break and give in to her control. On a good night, it would only take ten, and he would be perfectly pushed into his subspace. Tonight Jester was nearing thirty, her own palm starting to burn when finally Jester felt him give, his body fully relaxing in the ropes and his breath coming in pants that were quickly turning to sobs. Jester continued for another five with no mercy, landing particularly hard ones against where his thighs and ass met, marks for him to carry on for a day or two to remember.

Slowly she softened her blows as he started to cry, body settling simply taking what she gave him. Going from the chaos of untimed strikes to an easy rhythm she brought Caleb down from the height of the spanking and deeper into his subspace until all she was doing was rubbing those bright red cheeks as she let him catch his breath.

“Shhhhh, see now? Isn’t this better?” A satisfying sort of possessiveness settled over Jester, here was her good boy, all covered in her ropes and marks, now soft and pliant for her.

Caleb gasped a little but otherwise didn’t move as Jester leaned to place her cool lips in a soothing kiss against one particularly red and heated patch of skin.

“Give me a color, Cayleb,” she prompted gently when he didn’t answer her.

Caleb’s breath was ragged for a moment, “Yellow, please, a moment I-”

“Oh, Cayleb,” Jester immediately reached for the dagger she’d put with their toys only to be stopped by Caleb begging.

“Nein, please don't- just a moment, Mistress,” He wiggled a little, “Hold me?”

“Always,” Jester laid herself back over him, pushing his hair to the side to press little soft kisses across first the back of his neck and then his still wet cheeks, turning his head just enough to place one to his nose before meeting his lips. It was sweet, meant to comfort not arouse.

They stayed that way for just a minute, breathing together nose to nose until Caleb wiggled just a little, “I am ready to continue, please Mistress, grün,”

“Nothing is too tight? Nothing’s going numb?” Jester checked over her knots herself as she straightened.

“Nein, Mistress,” Caleb’s voice was more steady, and he did his best to arch within the ropes.

Jester looked back over to their toys in a moment of indecision. On the one hand, Caleb was already anticipating what she’d said, but Jester had made that plan with the thought it’d take more to have Caleb break and submit, “I’m going to leave the bed for just a moment, I’ll be right back, my good boy,”

Jester more felt than heard Caleb’s breath catch then still as she crossed the room. 

Quick, clever boy.

Changing out the plug she’d chosen for her favorite harness -with Caleb’s favorite toy in it, a thick and studded blue glass cock he’d had specially made in Zadash but enchanted himself; it stayed cool like her skin, and gave her just as much pleasure as him- she quickly strapped it on and returned to the bed.

“You look so good like this Cayleb, all tied up, covered in my marks and open for me,” Jester ran her hands all over him again, reaching around to roll his sensitive nipples as she pressed the length of her cock against his nicely warmed ass, “How am I supposed to resist you when you look like this?”

“You- _scheisse_ … You do not have to, Mistress,” Caleb was breathless again, trying to rock back against her but unable to.

“Mmmm, no I don’t have to,” Jester said, trailing her hands down to his desperate bound cock, stroking him lightly over the leather ties and gathering the steady drip of precum on her fingertips, “but I did already tell you what I was going to do,”

“Nein, please, Mistress let me pleasure yo-”

Caleb was cut off with a gasp as Jester pulled her fingers around, spreading his own wetness across his entrance, just rubbing for a moment before pressing one finger in.

“I don’t know, Cayleb...” Jester teased, taking a quick moment to pour slick on her other fingers and around his tight entrance as that first finger found his prostate with practiced ease, “You made me work for it tonight, do you really think you deserve to have me fuck you?”

“Please… Mistress please, let me pleasure you, you shouldn’t,” He gasped out a groan as Jester slid another finger in and then stopped all motion of her hand, “You shouldn’t have to make yourself cum, Mistress, when you have me to use,”

“Well when you put it that way,” She set to stretching him quicker, patience drying up fast in the face of how warm and soft he was around her fingers, how much better she knew he’d feel wrapped tight around her cock. 

Taking out her fingers Jester took a moment to just admire the lovely sight of his wet, desperate hole, drawing out his anticipation before pressing the head against him and wasting no time in slamming home. Which of them moaned louder she couldn’t tell, the hot velvet grip of him stealing away her breath and her hands found his hips in a savage grasp, nails digging into him as she pulled out slowly before slamming back in.

“Fuck, Cayleb… So good,” 

Beneath her Caleb was eagerly taking her cock, trying to press back to take more shaking a little as she picked up the pace, working herself quickly towards her first orgasm.

“Ah! Thank you, just want to be… want to be good for you, so bad, soooo,” Caleb moaned as Jester pressed hard against him and he could feel the wet heat of her spilling in him.

“You are so good for me Cayleb,” she purred, immediately returning to thrusting in him, slower this time, a sinful rolling of her hips and she bent over him, releasing his hips in favor of tangling one hand in his hair to pull his head up while the other reached below him to the straining length of his cock so hard still, “My good boy,”

Caleb was quickly reduced to little more than gasps and moans as Jester took her time building up to her next orgasm. Keeping his head pulled up she had free reign to suck and bite at his throat. Her other hand drifting between his desperate aching cock and his sensitive nipples, each teasing touch making his arch and jump against her, tightened more around her cock trying to milk another load from her. 

It didn’t take long.

Jester was just coming down from that high when she realized he was full shaking beneath her, her cock buried as far as it could go with her hips flush against his burning hot ass, “Give me a color, Cayleb,”

“Green!” He choked out, breathing harsh, “Please,”

“Please what Cayleb?” Jester asked with a wicked grin as she pulled almost all the way out of him.

“Ach- noooo please don’t, please…” Caleb tried desperately to push back.

“Is there something you want?”

As she spoke Jester trailed both her hands to his cock, one stroking slowly up and down while the other just brushed against where the main tie was. 

Caleb just whimpered.

“If you don’t use your words I can’t help you Cayleb,” her hand sped up and she pushed her cock back in an inch before pulling back again.

“Please… Mistress… let me cum, please, I need to cum with your cock pounding into me and you’re teeth in my throat,”

Jester couldn’t stop herself from slamming into him, a shiver racing up her back at the filthy words pouring from her boy’s mouth. With a growl she undid the leather wrapped around his penis, one hand shooting up to tangle again in his hair while the other gripped his hip again as she thrust into him with wild abandon.

“Cum for me Cayleb,” Jester demanded in his ear before giving her good boy exactly what he’d earned and buried her teeth into his throat the bright, coppery taste of his blood filling her mouth as she felt his body tense as he came, ass locking painfully tight around her cock and pulling another orgasm from her. Jester fucked him for another minute more enjoying the sounds he made from the overstimulation before slowly pulling her cock and her teeth out of him.

With a kiss, the wound on his neck knit back together, though shiny lines of scar tissue remained amongst the hickies, and Jester was whispering over and over to him as her shaking hands set to unraveling her ropework.

“Oh my sweet boy, so good, so perfect for me,” Jester rolled him onto his side, away from the rapidly cooling puddle of his cum. 

Fingertips traced the patterns left on his skin, finding every raw spot, and filing it away. In a minute she would get to that but for now, she just held Caleb close to her, his head tucked under her chin, his long limbs wrapped tightly around her body as he slowly came down, came back to himself. 

“There we go, come back to me Cayleb, you were so wonderful,” she murmured, keeping her voice low, hands stroking all over him until he finally spoke.

“Thank you, Jester,” he buried his head further into her, pressing a soft dry kiss to her collarbone. 

“You’re very welcome, Cayleb,” Jester giggled a little, kissing the top of his head. 

Jester knew if she felt so settled, so satiated down to her core, that he was too but still she had to ask, “How do you feel?”

“Good, _ja_ , good, floaty and well used,” 

“Any unbearably sore spots?” with a quick wave of her hand she cleaned the mess off the bed so she could role him to his back, loathe to have him leave her arms but determined to take care of those spots she’d felt.

One by one she leaned down and kissed the better, the tingling rush of the magic against his skin making Caleb twitch a little even as he sighed.

“Not anymore,”

“Good, will you be ok while I go put our toys away and get us something to eat?”

A beat of silence.

“Can it wait? Just another few minutes?” Already his arms were reaching out to pull her back to him and she went willingly, snuggling up against him and murmuring.

“Of course, take as long as you need my love, I’m right here and I’m so proud of you, so happy with you,”

As Caleb relaxed Jester turned her head to press a quick kiss to his chin. 

Everything else really could wait while she made sure her wizard was taken care of. 

**Author's Note:**

> Widogast’s Enchanted Strap  
> Wondrous Item, Rare (Requires Attunement)
> 
> A hefty studded dildo made of blue glass that keeps a cool temperature at all times, enchanted to allow the wearer to feel the glass like it was their own flesh and the ability to ejaculate into their partner.


End file.
